Sigmatropic hydrogen shifts in aryltetraphenylcyclopentadienes View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2016-02

AUTHORS

G. A. Dushenko, I. E. Mikhailov, O. I. Mikhailova, R. M. Minyaev, V. I. Minkin

ABSTRACT

Dynamic NMR has revealed intramolecular migrations of hydrogen atom over the periphery of the five-membered ring in 5-(p-tolyl)-1,2,3,4-tetraphenylcyclopentadiene in a deuteronitrobenzene solution with energy barrier ΔG180≠ = 24.8 kcal/mol. Quantum-chemical DFT calculations B3LYP/6-311++G** have shown that such migrations in 1,2,3,4,5-pentaphenylcyclopentadiene in the gas phase occur in a chiral conformation of propeller type by the mechanism of 1,5-sigmatropic hydrogen shifts with retention of configuration through asymmetric transition state with energy barrier ΔEZPE≠ = 25.9 kcal/mol. Enantiomers P and M can readily interconvert into each other (ΔEZPE≠ = 3.9 kcal/mol) owing to synchronous flip rotations of the phenyl groups. More... »

PAGES

350-355

References to SciGraph publications

Identifiers

URI

http://scigraph.springernature.com/pub.10.1134/s0012500816120028

DOI

http://dx.doi.org/10.1134/s0012500816120028

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1015742599


Indexing Status Check whether this publication has been indexed by Scopus and Web Of Science using the SN Indexing Status Tool
Incoming Citations Browse incoming citations for this publication using opencitations.net

JSON-LD is the canonical representation for SciGraph data.

TIP: You can open this SciGraph record using an external JSON-LD service: JSON-LD Playground Google SDTT

[
  {
    "@context": "https://springernature.github.io/scigraph/jsonld/sgcontext.json", 
    "about": [
      {
        "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/0306", 
        "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
        "name": "Physical Chemistry (incl. Structural)", 
        "type": "DefinedTerm"
      }, 
      {
        "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/03", 
        "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
        "name": "Chemical Sciences", 
        "type": "DefinedTerm"
      }
    ], 
    "author": [
      {
        "affiliation": {
          "alternateName": "Southern Scientific Center", 
          "id": "https://www.grid.ac/institutes/grid.465325.3", 
          "name": [
            "Southern Scientific Center, Russian Academy of Sciences, 344006, Rostov-on-Don, Russia"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Dushenko", 
        "givenName": "G. A.", 
        "id": "sg:person.015115321715.66", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.015115321715.66"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Southern Federal University", 
          "id": "https://www.grid.ac/institutes/grid.182798.d", 
          "name": [
            "Southern Scientific Center, Russian Academy of Sciences, 344006, Rostov-on-Don, Russia", 
            "Research Institute of Physical and Organic Chemistry, Southern Federal University, 344104, Rostov-on-Don, Russia"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Mikhailov", 
        "givenName": "I. E.", 
        "id": "sg:person.016631604463.46", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.016631604463.46"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Southern Scientific Center", 
          "id": "https://www.grid.ac/institutes/grid.465325.3", 
          "name": [
            "Southern Scientific Center, Russian Academy of Sciences, 344006, Rostov-on-Don, Russia"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Mikhailova", 
        "givenName": "O. I.", 
        "id": "sg:person.014137337701.03", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.014137337701.03"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Southern Federal University", 
          "id": "https://www.grid.ac/institutes/grid.182798.d", 
          "name": [
            "Research Institute of Physical and Organic Chemistry, Southern Federal University, 344104, Rostov-on-Don, Russia"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Minyaev", 
        "givenName": "R. M.", 
        "id": "sg:person.01047475616.15", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01047475616.15"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Southern Federal University", 
          "id": "https://www.grid.ac/institutes/grid.182798.d", 
          "name": [
            "Research Institute of Physical and Organic Chemistry, Southern Federal University, 344104, Rostov-on-Don, Russia"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Minkin", 
        "givenName": "V. I.", 
        "id": "sg:person.07535265367.87", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.07535265367.87"
        ], 
        "type": "Person"
      }
    ], 
    "citation": [
      {
        "id": "https://doi.org/10.1070/mc1997v007n02abeh000669", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1004509577"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/s0022-328x(03)00637-5", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1008567358"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/s0022-328x(03)00637-5", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1008567358"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1070/mc1999v009n06abeh001166", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1012849371"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1007/s11172-012-0233-0", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1016120864", 
          "https://doi.org/10.1007/s11172-012-0233-0"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/j.ccr.2011.02.001", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1022011553"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1071/ch9900281", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1025989525"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1070/mc1994v004n01abeh000325", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1031363740"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1070/mc1995v005n04abeh000491", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1036260358"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1007/bf02498157", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1037115280", 
          "https://doi.org/10.1007/bf02498157"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1007/bf02498157", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1037115280", 
          "https://doi.org/10.1007/bf02498157"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/acs.organomet.5b00842", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1055122845"
        ], 
        "type": "CreativeWork"
      }
    ], 
    "datePublished": "2016-02", 
    "datePublishedReg": "2016-02-01", 
    "description": "Dynamic NMR has revealed intramolecular migrations of hydrogen atom over the periphery of the five-membered ring in 5-(p-tolyl)-1,2,3,4-tetraphenylcyclopentadiene in a deuteronitrobenzene solution with energy barrier \u0394G180\u2260 = 24.8 kcal/mol. Quantum-chemical DFT calculations B3LYP/6-311++G** have shown that such migrations in 1,2,3,4,5-pentaphenylcyclopentadiene in the gas phase occur in a chiral conformation of propeller type by the mechanism of 1,5-sigmatropic hydrogen shifts with retention of configuration through asymmetric transition state with energy barrier \u0394EZPE\u2260 = 25.9 kcal/mol. Enantiomers P and M can readily interconvert into each other (\u0394EZPE\u2260 = 3.9 kcal/mol) owing to synchronous flip rotations of the phenyl groups.", 
    "genre": "research_article", 
    "id": "sg:pub.10.1134/s0012500816120028", 
    "inLanguage": [
      "en"
    ], 
    "isAccessibleForFree": false, 
    "isPartOf": [
      {
        "id": "sg:journal.1082681", 
        "issn": [
          "0012-5008", 
          "1608-3113"
        ], 
        "name": "Doklady Chemistry", 
        "type": "Periodical"
      }, 
      {
        "issueNumber": "2", 
        "type": "PublicationIssue"
      }, 
      {
        "type": "PublicationVolume", 
        "volumeNumber": "471"
      }
    ], 
    "name": "Sigmatropic hydrogen shifts in aryltetraphenylcyclopentadienes", 
    "pagination": "350-355", 
    "productId": [
      {
        "name": "readcube_id", 
        "type": "PropertyValue", 
        "value": [
          "4b01f474bfa7fa20c275cc6ab19f54d8a52925b8fae4a81a760a9da1de19597f"
        ]
      }, 
      {
        "name": "doi", 
        "type": "PropertyValue", 
        "value": [
          "10.1134/s0012500816120028"
        ]
      }, 
      {
        "name": "dimensions_id", 
        "type": "PropertyValue", 
        "value": [
          "pub.1015742599"
        ]
      }
    ], 
    "sameAs": [
      "https://doi.org/10.1134/s0012500816120028", 
      "https://app.dimensions.ai/details/publication/pub.1015742599"
    ], 
    "sdDataset": "articles", 
    "sdDatePublished": "2019-04-11T13:09", 
    "sdLicense": "https://scigraph.springernature.com/explorer/license/", 
    "sdPublisher": {
      "name": "Springer Nature - SN SciGraph project", 
      "type": "Organization"
    }, 
    "sdSource": "s3://com-uberresearch-data-dimensions-target-20181106-alternative/cleanup/v134/2549eaecd7973599484d7c17b260dba0a4ecb94b/merge/v9/a6c9fde33151104705d4d7ff012ea9563521a3ce/jats-lookup/v90/0000000367_0000000367/records_88239_00000000.jsonl", 
    "type": "ScholarlyArticle", 
    "url": "https://link.springer.com/10.1134%2FS0012500816120028"
  }
]
 

Download the RDF metadata as:  json-ld nt turtle xml License info

HOW TO GET THIS DATA PROGRAMMATICALLY:

JSON-LD is a popular format for linked data which is fully compatible with JSON.

curl -H 'Accept: application/ld+json' 'https://scigraph.springernature.com/pub.10.1134/s0012500816120028'

N-Triples is a line-based linked data format ideal for batch operations.

curl -H 'Accept: application/n-triples' 'https://scigraph.springernature.com/pub.10.1134/s0012500816120028'

Turtle is a human-readable linked data format.

curl -H 'Accept: text/turtle' 'https://scigraph.springernature.com/pub.10.1134/s0012500816120028'

RDF/XML is a standard XML format for linked data.

curl -H 'Accept: application/rdf+xml' 'https://scigraph.springernature.com/pub.10.1134/s0012500816120028'


 

This table displays all metadata directly associated to this object as RDF triples.

125 TRIPLES      21 PREDICATES      37 URIs      19 LITERALS      7 BLANK NODES

Subject Predicate Object
1 sg:pub.10.1134/s0012500816120028 schema:about anzsrc-for:03
2 anzsrc-for:0306
3 schema:author Nca66f659551647b5be13a6df028e6718
4 schema:citation sg:pub.10.1007/bf02498157
5 sg:pub.10.1007/s11172-012-0233-0
6 https://doi.org/10.1016/j.ccr.2011.02.001
7 https://doi.org/10.1016/s0022-328x(03)00637-5
8 https://doi.org/10.1021/acs.organomet.5b00842
9 https://doi.org/10.1070/mc1994v004n01abeh000325
10 https://doi.org/10.1070/mc1995v005n04abeh000491
11 https://doi.org/10.1070/mc1997v007n02abeh000669
12 https://doi.org/10.1070/mc1999v009n06abeh001166
13 https://doi.org/10.1071/ch9900281
14 schema:datePublished 2016-02
15 schema:datePublishedReg 2016-02-01
16 schema:description Dynamic NMR has revealed intramolecular migrations of hydrogen atom over the periphery of the five-membered ring in 5-(p-tolyl)-1,2,3,4-tetraphenylcyclopentadiene in a deuteronitrobenzene solution with energy barrier ΔG180≠ = 24.8 kcal/mol. Quantum-chemical DFT calculations B3LYP/6-311++G** have shown that such migrations in 1,2,3,4,5-pentaphenylcyclopentadiene in the gas phase occur in a chiral conformation of propeller type by the mechanism of 1,5-sigmatropic hydrogen shifts with retention of configuration through asymmetric transition state with energy barrier ΔEZPE≠ = 25.9 kcal/mol. Enantiomers P and M can readily interconvert into each other (ΔEZPE≠ = 3.9 kcal/mol) owing to synchronous flip rotations of the phenyl groups.
17 schema:genre research_article
18 schema:inLanguage en
19 schema:isAccessibleForFree false
20 schema:isPartOf N4786ffb0290e4914a3f5b6ca40a7a1de
21 N4a48606bb07a4467b81b2e294fc69e34
22 sg:journal.1082681
23 schema:name Sigmatropic hydrogen shifts in aryltetraphenylcyclopentadienes
24 schema:pagination 350-355
25 schema:productId N26260c2c748f4439818947169e52eb13
26 Ne00b164676fa4f59b025f9fe3482e3b4
27 Nf1d5f8c0a0574ae8b536eac5d1ad1ad2
28 schema:sameAs https://app.dimensions.ai/details/publication/pub.1015742599
29 https://doi.org/10.1134/s0012500816120028
30 schema:sdDatePublished 2019-04-11T13:09
31 schema:sdLicense https://scigraph.springernature.com/explorer/license/
32 schema:sdPublisher Ndb5525d32d0547168cc9e2e7565417cc
33 schema:url https://link.springer.com/10.1134%2FS0012500816120028
34 sgo:license sg:explorer/license/
35 sgo:sdDataset articles
36 rdf:type schema:ScholarlyArticle
37 N058dc9614f514cc3b1c0b58cda3a1f52 rdf:first sg:person.07535265367.87
38 rdf:rest rdf:nil
39 N26260c2c748f4439818947169e52eb13 schema:name dimensions_id
40 schema:value pub.1015742599
41 rdf:type schema:PropertyValue
42 N28e2c1271d3946c7ac84132f04d1a124 rdf:first sg:person.01047475616.15
43 rdf:rest N058dc9614f514cc3b1c0b58cda3a1f52
44 N4786ffb0290e4914a3f5b6ca40a7a1de schema:issueNumber 2
45 rdf:type schema:PublicationIssue
46 N4a48606bb07a4467b81b2e294fc69e34 schema:volumeNumber 471
47 rdf:type schema:PublicationVolume
48 N62e9ecfadac34ead9f595562998e94e5 rdf:first sg:person.016631604463.46
49 rdf:rest N9f4f09dbae0f43e2a2b4e8c2facb440e
50 N9f4f09dbae0f43e2a2b4e8c2facb440e rdf:first sg:person.014137337701.03
51 rdf:rest N28e2c1271d3946c7ac84132f04d1a124
52 Nca66f659551647b5be13a6df028e6718 rdf:first sg:person.015115321715.66
53 rdf:rest N62e9ecfadac34ead9f595562998e94e5
54 Ndb5525d32d0547168cc9e2e7565417cc schema:name Springer Nature - SN SciGraph project
55 rdf:type schema:Organization
56 Ne00b164676fa4f59b025f9fe3482e3b4 schema:name doi
57 schema:value 10.1134/s0012500816120028
58 rdf:type schema:PropertyValue
59 Nf1d5f8c0a0574ae8b536eac5d1ad1ad2 schema:name readcube_id
60 schema:value 4b01f474bfa7fa20c275cc6ab19f54d8a52925b8fae4a81a760a9da1de19597f
61 rdf:type schema:PropertyValue
62 anzsrc-for:03 schema:inDefinedTermSet anzsrc-for:
63 schema:name Chemical Sciences
64 rdf:type schema:DefinedTerm
65 anzsrc-for:0306 schema:inDefinedTermSet anzsrc-for:
66 schema:name Physical Chemistry (incl. Structural)
67 rdf:type schema:DefinedTerm
68 sg:journal.1082681 schema:issn 0012-5008
69 1608-3113
70 schema:name Doklady Chemistry
71 rdf:type schema:Periodical
72 sg:person.01047475616.15 schema:affiliation https://www.grid.ac/institutes/grid.182798.d
73 schema:familyName Minyaev
74 schema:givenName R. M.
75 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01047475616.15
76 rdf:type schema:Person
77 sg:person.014137337701.03 schema:affiliation https://www.grid.ac/institutes/grid.465325.3
78 schema:familyName Mikhailova
79 schema:givenName O. I.
80 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.014137337701.03
81 rdf:type schema:Person
82 sg:person.015115321715.66 schema:affiliation https://www.grid.ac/institutes/grid.465325.3
83 schema:familyName Dushenko
84 schema:givenName G. A.
85 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.015115321715.66
86 rdf:type schema:Person
87 sg:person.016631604463.46 schema:affiliation https://www.grid.ac/institutes/grid.182798.d
88 schema:familyName Mikhailov
89 schema:givenName I. E.
90 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.016631604463.46
91 rdf:type schema:Person
92 sg:person.07535265367.87 schema:affiliation https://www.grid.ac/institutes/grid.182798.d
93 schema:familyName Minkin
94 schema:givenName V. I.
95 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.07535265367.87
96 rdf:type schema:Person
97 sg:pub.10.1007/bf02498157 schema:sameAs https://app.dimensions.ai/details/publication/pub.1037115280
98 https://doi.org/10.1007/bf02498157
99 rdf:type schema:CreativeWork
100 sg:pub.10.1007/s11172-012-0233-0 schema:sameAs https://app.dimensions.ai/details/publication/pub.1016120864
101 https://doi.org/10.1007/s11172-012-0233-0
102 rdf:type schema:CreativeWork
103 https://doi.org/10.1016/j.ccr.2011.02.001 schema:sameAs https://app.dimensions.ai/details/publication/pub.1022011553
104 rdf:type schema:CreativeWork
105 https://doi.org/10.1016/s0022-328x(03)00637-5 schema:sameAs https://app.dimensions.ai/details/publication/pub.1008567358
106 rdf:type schema:CreativeWork
107 https://doi.org/10.1021/acs.organomet.5b00842 schema:sameAs https://app.dimensions.ai/details/publication/pub.1055122845
108 rdf:type schema:CreativeWork
109 https://doi.org/10.1070/mc1994v004n01abeh000325 schema:sameAs https://app.dimensions.ai/details/publication/pub.1031363740
110 rdf:type schema:CreativeWork
111 https://doi.org/10.1070/mc1995v005n04abeh000491 schema:sameAs https://app.dimensions.ai/details/publication/pub.1036260358
112 rdf:type schema:CreativeWork
113 https://doi.org/10.1070/mc1997v007n02abeh000669 schema:sameAs https://app.dimensions.ai/details/publication/pub.1004509577
114 rdf:type schema:CreativeWork
115 https://doi.org/10.1070/mc1999v009n06abeh001166 schema:sameAs https://app.dimensions.ai/details/publication/pub.1012849371
116 rdf:type schema:CreativeWork
117 https://doi.org/10.1071/ch9900281 schema:sameAs https://app.dimensions.ai/details/publication/pub.1025989525
118 rdf:type schema:CreativeWork
119 https://www.grid.ac/institutes/grid.182798.d schema:alternateName Southern Federal University
120 schema:name Research Institute of Physical and Organic Chemistry, Southern Federal University, 344104, Rostov-on-Don, Russia
121 Southern Scientific Center, Russian Academy of Sciences, 344006, Rostov-on-Don, Russia
122 rdf:type schema:Organization
123 https://www.grid.ac/institutes/grid.465325.3 schema:alternateName Southern Scientific Center
124 schema:name Southern Scientific Center, Russian Academy of Sciences, 344006, Rostov-on-Don, Russia
125 rdf:type schema:Organization
 




Preview window. Press ESC to close (or click here)


...